Methanamine, N-methoxy-, hydrochloride (1:1) → 3-(1,3-Dimethyl-2,4-dioxo-5-phenyl-3,4-dihydro-1H-pyrrolo[3,4-d]pyrimidin-6(2H)-yl)-N-methoxy-N-methylpropanamide

Participants

Reaction Steps

Isopropylmagnesium bromide solution (2.9M, 3.03 mL, 8.79 mmol) was added slowly to a suspension of methyl 3-(1,3-dimethyl-2,4-dioxo-5-phenyl-3,4-dihydro-1H-pyrrolo[3,4-d]pyrimidin-6(2H)-yl)propanoate (Example 11.0 step 1) (1.5 g, 4.39 mmol) and commercially available N,O-dimethylhydroxylamine hydrochloride (0.514 g, 5.27 mmol) in THF (50 mL) at 0° C. The mixture was warmed to room temperature and stirred for 30 mins. A further portion of isopropylmagnesium bromide solution (2.9M, 3.03 mL, 8.79 mmol) was added slowly and the mixture stirred for a further 60 mins. The reaction was quenched with saturated NH4Cl(aq) and extracted with EtOAc (2×). The combined organic extracts were washed with brine, dried over sodium sulfate and evaporated under vacuum. Purification by chromatography on silica, eluting with 50-100% EtOAc/hexane, then 1-8% MeOH/EtOAc afforded the title compound.

Provenance & Evidence